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α-Cyano-4-hydroxycinnamic Acid - 10mM in DMSO, high purity , CAS No.28166-41-8, Inhibitor of mitochondrial pyruvate carrier 1;Inhibitor of mitochondrial pyruvate carrier 2

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C422987
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C422987-1ml
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$69.90

Monocarboxylic acid transport inhibitor

Basic Description

Synonyms alpha-cyano-4-hydroxycinnamic acid | 28166-41-8 | a-Cyano-4-hydroxycinnamic acid | alpha-Cyano | 122520-77-8 | (2E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid | CHCA | (E)-2-cyano-3-(4-hydroxyphenyl)acrylic acid | (E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid | alpha-
Specifications & Purity Moligand™, 10mM in DMSO
Biochemical and Physiological Mechanisms Monocarboxylic acid transport (MCT) inhibitor. Exhibits antitumoral and antiangiogenic activity in gliomas in vivo . Decreases glycolytic metabolism, migration, and invasion in U251 cells. Enhances the effect of the DNA-methylating antitumor agent temozol
Storage Temp Store at -80°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Grade Moligand™
Action Type INHIBITOR
Mechanism of action Inhibitor of mitochondrial pyruvate carrier 1;Inhibitor of mitochondrial pyruvate carrier 2
Product Description

Product Introduction

α-Cyano-4-hydroxycinnamic acid is the commonly used matrix for analyzing peptides by matrix-assisted laser desorption/ionization mass spectrometry. It inhibits the monophenolase activity and diphenolase activity of mushroom tyrosinase.

Application

α-Cyano-4-hydroxycinnamic acid (CHC) was used in encapsulation of CHC into NaY zeolite. It was used as matrix to investigate the activity of the paclitaxel derivatives using several well-established in vitro angiogenesis assays.

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Phenylpropanoids and polyketides
Class Cinnamic acids and derivatives
Subclass Hydroxycinnamic acids and derivatives
Intermediate Tree Nodes Not available
Direct Parent Hydroxycinnamic acids
Alternative Parents Coumaric acids  Cinnamic acids  1-hydroxy-2-unsubstituted benzenoids  Benzene and substituted derivatives  Nitriles  Monocarboxylic acids and derivatives  Carboxylic acids  Organopnictogen compounds  Organic oxides  Hydrocarbon derivatives  Carbonyl compounds  
Molecular Framework Aromatic homomonocyclic compounds
Substituents Cinnamic acid - Coumaric acid - Coumaric acid or derivatives - Hydroxycinnamic acid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Benzenoid - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Carbonitrile - Nitrile - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Aromatic homomonocyclic compound
Description This compound belongs to the class of organic compounds known as hydroxycinnamic acids. These are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
External Descriptors phenols - nitrile - monohydroxycinnamic acid

Associated Targets(Human)

MPC2 Tbio Mitochondrial pyruvate carrier 2 (0 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
MPC1 Tbio Mitochondrial pyruvate carrier 1 (0 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SiHa (2051 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HCT-116 (91556 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HeLa (62764 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SLC16A1 Tchem Monocarboxylate transporter 1 (146 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
GPR35 Tchem G-protein coupled receptor 35 (2643 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SLC16A3 Tchem Monocarboxylate transporter 4 (196 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SLC16A7 Tchem Monocarboxylate transporter 2 (11 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Mus musculus (284745 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
KCNK2 Potassium channel subfamily K member 2 (9 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name (E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
INCHI InChI=1S/C10H7NO3/c11-6-8(10(13)14)5-7-1-3-9(12)4-2-7/h1-5,12H,(H,13,14)/b8-5+
InChIKey AFVLVVWMAFSXCK-VMPITWQZSA-N
Smiles C1=CC(=CC=C1C=C(C#N)C(=O)O)O
Isomeric SMILES C1=CC(=CC=C1/C=C(\C#N)/C(=O)O)O
WGK Germany 3
Molecular Weight 189.17
Beilstein 3271430
Reaxy-Rn 8201999
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8201999&ln=

Certificates(CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

Melt Point(°C) 245-250℃
Molecular Weight 189.170 g/mol
XLogP3 1.400
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 2
Exact Mass 189.043 Da
Monoisotopic Mass 189.043 Da
Topological Polar Surface Area 81.300 Ų
Heavy Atom Count 14
Formal Charge 0
Complexity 292.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 1
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 1
Covalently-Bonded Unit Count 1

Citations of This Product

1. Xiaoyu Yuan, Jiayi Song, Han Wang, Wenkang Zhang, Ying Liu, Ping Su, Yi Yang.  (2024)  Dual-functionalized two-dimensional metal–organic framework composite with highly hydrophilicity for effective enrichment of glycopeptides.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,  1232  (123920). 
2. Chenhui Lu, Haodong Wei, Lizhi Xu, Wen-Long Wang, Cheng Yang, Xueli Shi, Hui Gao, Yong-Wei Feng, Jianzhong Zhou, Yi Zhang.  (2024)  Enrichment of sialic acid-containing casein glycomacropeptide in protein hydrolysates using phenylboronic acid-functionalized mesoporous silica nanoparticles.  TALANTA,  267  (125174). 
3. Lei Wang, Yuhao Han, Yaqi Zhang, Haoyuan Geng, Zihan Zhu, Panpan Chen, Xiaoqing Cui, Xiao Wang, Chenglong Sun.  (2023)  In-depth profiling of carbohydrate isomers in biological tissues by chemical derivatization-assisted mass spectrometry imaging.  ANALYTICA CHIMICA ACTA,  1278  (341741). 
4. Xirui Duan, Hailong Tian, Shuwen Zheng, Jianmei Zhu, Chan Li, Bo He, Lei Li, Hao Jiang, Shuaijun Lu, Yumei Feng, Gary T. Bentley, Wei Zhang, Canhua Huang, Wei Gao, Na Xie, Ke Xie.  (2023)  Photothermal-Starvation Therapy Nanomodulator Capable of Inhibiting Colorectal Cancer Recurrence and Metastasis by Energy Metabolism Reduction.  Advanced Healthcare Materials,    (2300968). 
5. Xiaolu Hu, Lan Yu, Yatong Li, Xiaoxi Li, Yimeng Zhao, Lijuan Xiong, Jiaxuan Ai, Qijun Chen, Xing Wang, Xiaoqing Chen, Yinying Ba, Yaonan Wang, Xia Wu.  (2023)  Piperine improves levodopa availability in the 6-OHDA-lesioned rat model of Parkinson's disease by suppressing gut bacterial tyrosine decarboxylase.  CNS Neuroscience & Therapeutics,     
6. Qi Meng, Jia Tan, Weifang Tong, Changxiao Chen, Zhendong Liu, Sainan Liu, Meifang Wang, Ziyong Cheng, Binbin Ding, Ping'an Ma, Jun Lin.  (2023)  Ultrafast self-assembled supramolecular nanoparticles for enhanced chemodynamic therapy and ferroptosis through lactic acid metabolism regulation.  CHEMICAL ENGINEERING JOURNAL,  471  (144563). 
7. Xian Wang, ShiJiang Qin, Guocan Zheng, Weili Wei, Fang Li, Yao Luo, JinJing Tang, Kai Zhou.  (2023)  Two-dimensional boron nanosheets for selective enrichment and detection of cis-diol compounds by surface-assisted laser desorption/ionization time-of-flight mass spectrometry.  JOURNAL OF CHROMATOGRAPHY A,  1705  (464142). 
8. Wenting Li, Shikai Liu, Yangyang Zhang, Jialing Zhou, Rumin Li, Shili Gai, Lei Zhong, Piaoping Yang.  (2023)  Dual-inhibition of lactate metabolism and Prussian blue-mediated radical generation for enhanced chemodynamic therapy and antimetastatic effect.  Nanoscale,  15  (20): (9214-9228). 
9. Liuying He, Xiao Wang, Junyu Chen, Yuze Li, Liping Wang, Caiqiao Xiong, Zongxiu Nie.  (2022)  Biofluids Metabolic Profiling Based on PS@Fe3O4–NH2 Magnetic Beads-Assisted LDI-MS for Liver Cancer Screening.  ANALYTICAL CHEMISTRY,  94  (29): (10367–10374). 
10. Wenya Shao, Ying Sun, Hang Su, Qianqian Sun, Zian Lin.  (2022)  4-Mercaptobenzoic acid-assisted laser desorption/ionization mass spectrometry for sensitive quantification of cesium and strontium in drinking water.  RAPID COMMUNICATIONS IN MASS SPECTROMETRY,  36  (17): (e9342). 
11. Shuzhen Dou, Zhongshun Wang, Qiye Chen, Nan Lu.  (2022)  One-step fabrication of high-density Si nanotips as SALDI-MS substrate for highly sensitive detection.  SENSORS AND ACTUATORS B-CHEMICAL,  359  (131578). 
12. Yuhao Han, Panpan Chen, Zhichao Li, Xiao Wang, Chenglong Sun.  (2022)  Multi-wavelength visible-light induced [2+2] cycloaddition for identification of lipid isomers in biological samples.  JOURNAL OF CHROMATOGRAPHY A,  1662  (462742). 
13. Ma Yuanyuan, Ye Zhongju, Zhang Chen, Zhao Yanjun, Luo Hai-bin, Xiao Lehui.  (2022)  Curved carbon photo-oxygenation catalysts for the suppression and nanoscopic imaging of β-amyloid peptides fibrillation.  Nano Research,  15  (4): (3387-3397). 
14. Cong Wang, Shao-Yi Jia, You Han, Yang Li, Yong Liu, Hai-Tao Ren, Song-Hai Wu, Xu Han.  (2021)  Selective Oxidation of Various Phenolic Contaminants by Activated Persulfate via the Hydrogen Abstraction Pathway.  ACS ES&T Engineering,  (9): (1275–1286). 
15. Chen Ya-Shun, Feng Yu-Qi.  (2022)  Rapid Determination of Endogenous 20-Hydroxyecdysone in Plants on MALDI-TOF/TOF Mass Spectrometry via Chemical Labeling Based on Boronate Affinity.  Journal of Analysis and Testing,  (3): (318-326). 
16. Chenglong Sun, Shuangshuang Ma, Lili Li, Daijie Wang, Wei Liu, Feng Liu, Lanping Guo, Xiao Wang.  (2021)  Visualizing the distributions and spatiotemporal changes of metabolites in Panax notoginseng by MALDI mass spectrometry imaging.  Journal of Ginseng Research,  45  (726). 
17. Qianqian Sun, Shasha Zhang, Weini Huang, Ran Wang, Zihan Chen, Zongwei Cai, Zian Lin.  (2021)  4-Mercaptobenzoic acid as a MALDI matrix for highly sensitive analysis of metals.  ANALYST,  146  (5): (1543-1547). 
18. Xiao-Cong Zhang, Song-Hai Wu, Shao-Yi Jia, Cong Wang, Shi-Wei Sun, Xiang-Ming Wang, Zi-He Meng, Yi-Ying Lin, Yong Liu, Hai-Tao Ren, Xu Han.  (2020)  Turning thiophene contaminant into polymers from wastewater by persulfate and CuO.  CHEMICAL ENGINEERING JOURNAL,  397  (125351). 
19. Chen Ya-Shun, Xiao Hua-Ming, Wang Tian-Qi, Yu Lei, Feng Yu-Qi.  (2019)  A boronic acid modified binary matrix consisting of boron nitride and α-cyano-4-hydroxycinnamic acid for determination of cis-diols by MALDI-TOF MS.  MICROCHIMICA ACTA,  186  (8): (1-8). 
20. Chen Ya-Shun, Ding Jun, He Xiao-Mei, Xu Jing, Feng Yu-Qi.  (2018)  Synthesis of tellurium nanosheet for use in matrix assisted laser desorption/ionization time-of-flight mass spectrometry of small molecules.  MICROCHIMICA ACTA,  185  (8): (1-9). 
21. Jun Ding, Simin Liu, Hua-Ming Xiao, Tian-tian Ye, Ping Zhou, Yu-Qi Feng.  (2017)  Matrix-assisted laser desorption/ionization mass spectrometry for the analysis of polyamines in plant micro-tissues using cucurbituril as a host molecule.  ANALYTICA CHIMICA ACTA,  987  (56). 
22. Hai-Jiao Zheng, Jiu-Tong Ma, Wei Feng, Qiong Jia.  (2017)  Specific enrichment of glycoproteins with polymer monolith functionalized with glycocluster grafted β-cyclodextrin.  JOURNAL OF CHROMATOGRAPHY A,  1512  (88). 
23. Wenjuan Zhang,Liyan Jiang,Li Fu,Qiong Jia.  (2018-12-30)  Selective enrichment of glycopeptides based on copper tetra(N-carbonylacrylic) aminephthalocyanine and iminodiacetic acid functionalized polymer monolith..  Journal of separation science,  42  ((5)): (1037-1044). 
24. Zhengge Chen, Yi Hong, Futao Lin, Xiongfei Zha, Fengcheng Lin, Yang Li, Bin Hu, Qi Huang, Lei Li, Zhengxu Huang, Li Ding, Zhen Zhou.  (2025)  An Ultra-High-Resolution Mass Spectrometer with an Intermediate-Pressure Matrix-Assisted Laser Desorption/Ionization Source.  ANALYTICAL CHEMISTRY,  97  (13): (7369-7377). 
25. Xintong Zhao, Juan Ren, Ze Wang, Xiangfeng Chen.  (2024)  Analyzing noncovalent interactions between notoginseng saponins and lysozyme by deposition scanning intensity fading MALDI-TOF mass spectrometry.  JOURNAL OF MASS SPECTROMETRY,  59  (7): (e5058). 
26. Jiming Wei, Ling Li, Yun Shi, Juncheng Liu, Jiagen Lv, Tuanrui Dong.  (2024)  Cater to the call of on-site, quantitative, and low-cost food formaldehyde detection: A paper-based sensor by timing Congo red decoloration.  FOOD CONTROL,  160  (110321). 
27. Jiahui Yan, Haoyu Chen, Carlos F. Guimarães, Rui L. Reis, Zhihua Zhu, Tianyi Wang, Fenglan Zhang, Yaqian Lv, Qihui Zhou, Xiaoying Kong, Jinsheng Shi.  (2024)  Cu+/Ca2+ Dual-Overload Strategy Assisted by Metabolic-Symbiotic-Destruction for Tumor Apoptosis and Tumor Immune Activation.  ADVANCED FUNCTIONAL MATERIALS,    (2403245). 
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29. Huan Li, Chang Chen, Xinzhu Chen, Jiale Liu, Chen Luo, Huilin Chen, Xiaoyu Geng, Zheng Pan.  (2025)  Identification of active ingredients from Lamiophlomis rotata that increase wound repair in mouse skin.  BRITISH JOURNAL OF PHARMACOLOGY,     
30. Jingtong Zhai, Yalei Wang, Jiaxin Lu, Chunning Chen, Jiaqi Liu, Hongkun Zhao, Nan Lu.  (2024)  Improving performance of SALDI-MS by regulating density of plasmonic nanoparticles.  SENSORS AND ACTUATORS B-CHEMICAL,  409  (135560). 
31. Dong Junliang, Ding Jindong, Luo Shifan, Li Ruoshui, Wang Yi, Xiao Bing, Pei Yuxin, Chen Xiaoyuan, Sun Wenjing, Pei Zhichao.  (2025)  Remodeling tumor microenvironment using prodrug nMOFs for synergistic cancer therapy.  JOURNAL OF NANOBIOTECHNOLOGY,  23  (1): (1-14). 
32. Cui Xiaoqing, Geng Haoyuan, Guo Huanying, Wang Lei, Zhu Zihan, Zhang Yaqi, Chen Panpan, Wang Xiao, Sun Chenglong.  (2024)  Visualizing the transdermal delivery of berberine loaded within chitosan microneedles using mass spectrometry imaging.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,  416  (29): (6869-6877). 

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